Why aren’t liberals funny? And how come conservative columnist David Brooks, formerly a stylish, witty, sharp-eyed writer, got to be such a plodding, stuffed-shirt prig when he went to work for a liberal publication?

Brooks’s book Bobos in Paradise is an example of an old-fashioned, way-we-live-now sociology—drawing the great social caricature—that is hardly practiced anymore (sociology, which used to be aligned with journalism, is now a quantitative discipline). His subject was middle-class identity and particularly, even though he’s a conservative, liberal-middle-class identity. As an observer of manners, Brooks was a little hyperbolic, a little reductive, and clever to a fault.

But then he went to the New York Times op-ed page. The Times, temperamentally resistant to the hyperbolic, the reductive, the too clever, took Brooks’s style away. Sociology without style is pomposity.

The complicated condition for liberals, or, anyway, for liberal wits and stylists, is that so much of the liberal media—the constricting liberal media—has defaulted to a kind of consensus *Times-*ness. Hence, in defensive mode, and in a careful estimation of our market opportunities, we are all—we well-employed, Ivy League–ish, culturally engaged, upper-middle-class chattering types in the mainstream news media—self-serious, earnest, striving, humorless, correct people, seeking to become ever more earnest, faultless, evenhanded. We’re Hillary (or we’re her base, and she’s courting us by becoming as worthy and flat as we are).

Not to put too fine a point on it, but liberals, in their desperate quest to be taken seriously, are the new conservatives.

Conservative opinionists in the burgeoning right-wing media—from Fox to talk radio to Rupert Murdoch’s Weekly Standard to the Wall Street Journal editorial page—are, on the other hand, often facile, funny, irreverent, eccentric, jaunty, pithy, as well as aggressive and wrongheaded (that improbable creature Ann Coulter is all those things), as well as operatic (Terri Schiavo was an opera). As well as, on occasion, inebriated. (The character note of a liberal these days is sobriety—no drinks, no carbs, no jokes. The conservatives run amok while the liberals are corporatized.)

Obviously, conservatives have reason to enjoy themselves, while liberals do not. But then, too, it may reasonably be the conservatives’ sense of verbal sport, of going too far, of showing off, that’s helped get them into their catbird seat. And, conversely, the liberals’ dullness and depressiveness—“little constipated souls,” in the recent description by Ben Bradlee, who is from the liberal media’s jaunty age—that’s contributed to their fate.

So why no oomph? No joy? No jokes?

In the exception-that-proves department, every liberal jumps up at this point demanding, “What about Jon Stewart?”

“And Maureen Dowd.”

“And,” add a few liberals in rarefied radio markets, “Air America and Al Franken.”

“Andy Borowitz!”

“Wonkette.”

“Michael Moore” (but with lessening enthusiasm—more and more embarrassingly he mistakes himself for a serious fellow).

These are the humor anomalies (pretty much the sum total of the humor anomalies). The genre-ists. It’s liberal comedy.

This is part of the liberal-journalism ethos. Editors and libel lawyers insist: if you mean it to be funny, you have to make it clear that it’s humor. Literalism—that pre-Asperger’s condition of wonks everywhere—is part of liberalism.

The conservatives have no appointed clowns. Rather, exaggeration is built into their argument. Is it shtick or isn’t it? Peggy Noonan is as exaggerated as Maureen Dowd, but she isn’t regarded as the in-house “crazy lady.” The talk-radio screed is as amusing as it is incendiary—it’s equal parts knee slap and outrage. Seriousness, the conservatives recognize, is, or ought to be, a fluid substance. Here’s the answer to the elemental question: Why can’t liberals do talk radio? Because they don’t know how to tease.

The most enjoyable conversations I have had about modern media—not often an enjoyable subject—have been with Roger Ailes, the Fox mastermind. He’s having fun. He’s bad. He’s a tease. He’s out to provoke. To create conflict rather than avoid it.

Does that mean he’s not serious? Well … Ailes is sly, charming, sometimes far-fetched, and irresistibly cynical about everybody’s motives and everybody’s virtue. Whereas we liberals are achingly serious—always. We’re good boys.

Good-boyism is partly about market conditions. It’s about getting a job. The fewer the jobs, the better the boy you have to be. Conservative media is a growing market; liberal media is a dwindling one. In the last decade or so, the conservatives have created all sorts of new and moneymaking opinion media. Whereas liberals have created only—I’ve really racked my brains here—Slate.

Slate?

Slate—the Microsoft-supported online magazine developed by liberal-media doyen Michael Kinsley, which has just been sold, at a great premium, to the Washington Post Company—is liberal media targeted at other people in the liberal media. Or, even more finely, targeted at other people in the liberal media who are concerned about issues such as the liberal media. (Various blogs, including Mickey Kaus’s O.C.D.-like reading and rereading of the liberal media, are connected to Slate, and many other liberal blogs are clearly being written to gain the attention of Slate.)

With revenues of about $6 million a year, Slate is, in size and reach, insignificant. But in terms of sensibility, it’s made it big—its self-importance can’t be denied. It’s faithfully Ivy League (the liberal media in its heart of hearts is made up of people who went to Harvard or who wish they’d gone to Harvard). Its cloying tone and manner strictly high-S.A.T. We’re smart people communing with like-minded smart people, marveling together at the quaint habits of the regular people. We’re here, the Slate people insist, because we have a contribution to make to the intellectual wealth of the world. It’s our duty. (The last time I saw *Slate’*s current editor, Jacob Weisberg, an ambitious climber up the liberal-media ladder, was at a crowded bar at the Democratic convention in Boston. I’d gotten into the bar because I’d cut out early on John Edwards’s vacuous acceptance speech. Weisberg, because he’d uselessly and diligently weathered the speech, was trapped, craning his neck, on the other side of the velvet rope. Said Weisberg, with apparent incredulity, “You walked out on the vice-presidential acceptance speech?”)

I have never actually met anyone who has read Slate who hasn’t at one time worked at Slate or considered hiring someone who might have worked at Slate.

That is sort of the point. Slate, which came into being as an experiment in new media, has become best known for the fact that many people who have worked at Slate have graduated into jobs in the old liberal media. If you are in the old liberal print media, and you need to hire somebody, the first place you look is Slate (this is not hyperbole; this is how it works, really). In other words, the primary purpose of the only new form of liberal media is to train people to work in the old liberal media.

The real problem with Slate is that nobody who works at Slate actually wants to be working at Slate. The people who work at Slate are not people who get pleasure out of telling their parents they work for an online magazine. Rather, the kind of people who work at Slate want to be working at the Times. They may not really even want to be in the media or news or writing business: they just want to be at The New York Times. (The reason The Washington Post bought Slate has not a little to do with the competition between the Times and the Post and this sense of Slate as the New York Times farm team.)

The hegemony of the Times in liberal journalism is a remarkable development. A generation ago you had a national liberal media (called the media, rather than the liberal media) that consisted of powerful network news operations with dizzying resources, a catchall of independent *Zeitgeist-*tracking magazines with lots of buzz and glamour, two newsweeklies concentrating on news and opinion rather than, as they do now, family and lifestyle stuff, a more or less independent public television, a (more) vigorous author-driven book business, as well as the Times. But now you have only the Times and its sonorous echo, NPR (the Post, outside of its impulsive purchase of Slate, has become a strictly regional publication).

The Times defines nearly the sum total of liberal respectability—and opportunity. It’s the employer of first choice and last resort. The Times is the market. Your paramount job as a provider of liberal opinion and commentary is to home in on the Times sensibility—get on that page.

But back to making jokes. Part of the issue here is that the Times, having sucked everything into its wake, can’t admit to having done this. The Times, because it is liberal, has to be on the side of multiple voices. It can’t acknowledge its domination, its hegemony—it can’t even acknowledge that it is liberal (because liberals believe that being liberal puts them at a higher station of fairness and probity). Indeed, by having more or less successfully extended its franchise across the nation, the Times has to insist even more firmly on its neutrality and transparency. It can’t wink the way Fox winks. It can’t enjoy itself (the fact that so many people at the Times are depressed people might have something to do with this).

Conservatives talk about being conservative all of the time. Conservatives are obsessed with their own identity—and eccentricities. It’s like talking about being Jewish—or like the way Jews once talked about being Jewish. It’s not just defining. It’s … funny.

Liberals never talk about being liberals—about the oddness that might make them unique and interesting. Mindful of their constant bad press, liberals—self-conscious press hounds one and all—don’t like to admit to being liberals (and as for the people who do admit to being liberals, you understand why others wouldn’t want to admit to being that).

It’s a pretty severe humor limitation when you can’t be funny about yourself.

My friend James Atlas, who has spent a long career in the liberal media, has just written a book called My Life in the Middle Ages, which is about, among other things, the pitiable and embarrassing angsts of a career in the liberal media. It’s an old-style (read “Jewish”), self-lacerating humor—no matter how much crummy success I’ve achieved, I’m a hideous failure—which has made, I detect, lots of people in the liberal media, who believe they are actually big successes, uncomfortable.

Jim’s real subject is status—that essential, and perhaps most difficult, liberal issue. It is the liberals’ shameful place (our Santa Barbara Neverland). I once got Jim into trouble by recounting a conversation that he and I have often had about how much money it takes to be a Manhattan liberal. Some time back Jim had estimated that it required a minimum annual income of $350,000 to maintain a family of four in middle-class-liberal style. I quoted him as having revised that upward to $500,000 (this was three or four years ago—what with real-estate increases, I’d push it up to $650,000 now), which seemed hilarious to me, Jim and I doing such desperate and slapdash accounting.

Now, killing the joke, I can explain why this ought to be funny: Talking about money when you’re not supposed to talk about money is funny. Trying to quantify status when you’re not supposed to quantify it (it’s just supposed to descend on you; you’re supposed to just deserve it, apparently) is funny. Saying in public anything that is supposed to be merely whispered in private is funny. And talking about this at all indicates nothing so much as how hopelessly small-time we are. But this comment caused Jim piles of grief. For many people in the greater liberal media this comment meant that Jim was … “status-conscious.” And a double vulgarian for discussing it openly. (In part for making such stabs at status-breaching humor, Jim details, wittily, in his book how he came to be fired from The New Yorker, that even higher liberal apogee than the Times.)

Indeed, in what might be interpreted as a not unimportant reading of the tea leaves of journalistic standards and practices, the Times Book Review recently gave prominent notice to a book (the kind of book—just a compendium of interviews, and a “paperback original” at that—that the Times usually deals with perfunctorily) which explicitly rejects the meaning and humor that Jim Atlas and, in the past, David Brooks—and, in some sense, every writer who has ever made a joke—have found in the issue of status.

The book, The New New Journalism, edited by Robert Boynton, who teaches N.Y.U. undergraduates how to write journalism for magazines (one hopes that he is not telling his students that there are actually journalism jobs at magazines these days), and reviewed by *Slate’*s media critic, Jack Shafer (an ever vigilant, indefatigable school-monitor type), means to formally revise the long-faded movement of *Zeitgeist-*defining journalists of the 60s and 70s (Tom Wolfe, Joan Didion, Norman Mailer, Truman Capote, Hunter Thompson, et al.), once called the “New Journalism.”

The New New Journalism (exemplified by Eric Schlosser’s deadly earnest Fast Food Nation, and Newjack, Ted Conover’s less-than-Dostoyevskian tour of a New York State prison as a pretend prison guard) rejects, according to Boynton, the New Journalism’s sociological concern with status. Rather, the primary subject of these new middle-class liberal journalists is … “the disenfranchised.” These New New Journalists, says Boynton, “consider class and race, not status, the primary indices of social hierarchy.”

Where practitioners of the old New were stylists, practitioners of the New New, according to the book, are focused on facts, eschewing what the Times dismisses as mere “fancy prose style.” The book discusses at great and reverential length the cult of John McPhee, a writer of fabled factuality and unstylishness, who, I would wager, has seldom been read to the end by anybody other than his acolytes, called McPhinos, many of whom took his class at Princeton and are now the New Newists.

Indeed, nonfiction writing, as it disappears from the commercial world, has made it big on campus. It’s called literary nonfiction. No jokes please, we’re serious.

Meanwhile, it’s been a year since the very correct and humorless Adam Moss, a former editor of The New York Times Magazine, took over New York magazine (I used to work at New York and left shortly before Moss arrived), a longtime venue for acute status journalism.

Now, New York has always been, in a sense, the un-Times place for liberal journalists, even the anti-Times (New York was spun off of the *Times’*s great lost competitor the New York Herald Tribune). I once tried to interview Times publisher Arthur Sulzberger Jr. for New York. But he refused, explaining, with his signature subtlety, “I hate New York magazine.”

New York serves liberal journalism in tabloid form. Its seminal interests have been position, hierarchy, power (both how to get more and how to make fun of people who were getting more). About which subjects it sought—often by way of exaggeration, metaphor, embellishment, gossip, and self-evident rapaciousness—to be entertaining, amusing, provocative, informative (in that order). If often pleasurable, New York was never quite respectable.

The change in the weekly since Moss—in addition to editing the Times Magazine for many years, he is also one of Sulzberger’s close friends—took over has been the most radical in *New York’*s near-40-year history: It’s become estimable. Praiseworthy (praising and reading are different, often inimical functions). Respectable—if no longer pleasurable. (It’s now owned by banker Bruce Wasserstein, to whom respectability may be worth more than money. Note: I was part of another group, one with more commercial intentions, which tried to buy New York.) With more words and smaller type, it’s hard work too—but good for you.

It’s repositioned itself as a worthy satellite of The New York Times. Like Slate, it will undoubtedly graduate lots of people to the Times. It’s quality. Self-conscious quality (perhaps all quality is). Ivy League quality.

But it isn’t funny. Not in the least. It’s completely in earnest. It’s serious about its job, grim in its efforts to elevate the metropolitan-area upper middle class.

Now I am getting older, moving deeper, with my friend Atlas, into the middle ages. So it may be that I am missing the new trend. THE NEW EARNESTNEST the old New York magazine might have headlined it. MEET THE NEW OLD FOGIES. I’d have enjoyed a light essay on the subject by David Brooks.

Except that, judging by the commercial health of the liberal media—not least of all its systemic inability to get anybody under middle age interested in it—it may be that all the earnest, respectability-seeking old fogies are on the inside working for the liberal media while the wisecracking vulgarians are on the outside ignoring it.

The problem may be that we liberals are by temperament job seekers rather than entrepreneurs. We’re just not outsiders. So if the Times is the great and encompassing and growing liberal info-and-opinion corporation—the only one left—then we’ve got to make ourselves attractive to it.

Pistols needn’t apply.

Michael Wolff, a Vanity Fair contributing editor, is the author of Autumn of the Moguls (HarperBusiness) and Burn Rate: How I Survived the Gold Rush Years on the Internet (Simon & Schuster).